The Madison St. Chukka Boot No. 5927 RTW

  • Uppers: Cognac Luxe Calf
  • Burnishing: Light
  • Lining: Brown Calf Leather
  • Sole: Cognac Hand-Painted Leather
  • Outsole: Brown
  • City Welt
  • Last: The 312 – Featuring a Rounded Toe for a Traditional English Style
  • Blake Stitch Construction

Handcrafted in Spain

  • Lace-ups, boots, and sneakers tend to fit true to size.
  • Loafers, Belgian slippers, boat shoes, and drivers tend to run a 1/2 size small.
  • If you are between sizes, order the larger size and request our custom insoles
  • Don’t forget to try the FeetSizer App!

More Information Available Here

$399.00

Dry Alive Custom Cut Insoles

Step into refined craftsmanship with the Madison St. Chukka Boot No. 5927. Built on the 312 last, this boot features a rounded toe that nods to traditional English styling while staying versatile enough for both tailored and casual wear. It’s a boot designed to move with you, from the office to a weekend out, without ever looking out of place.
The upper is crafted from Cognac Luxe Calf leather, treated with a light burnishing that adds depth and character to the finish. This subtle shading catches the light differently with every step, giving the leather a richness that develops further with age and wear. Inside, a brown calf leather lining offers a soft, breathable layer against your foot, reducing friction and keeping you comfortable through long days on your feet.
The sole is where this boot truly sets itself apart. Hand-painted in cognac, each sole carries a one-of-a-kind finish that no machine can replicate. This is paired with a brown outsole and a city welt, a detail that adds structure and a clean, tailored edge to the boot’s silhouette. Together, these elements create a boot that reads as polished without feeling stiff or overworked.
Underneath, Blake stitch construction keeps the profile slim and lightweight, unlike bulkier welted alternatives. This stitching method also allows for closer contact between your foot and the ground, giving you a more natural stride and better flexibility as the leather breaks in.
Every pair is handcrafted in Spain, built by artisans who understand the value of precision and are fully devoted to their craft. From the cut of the leather to the final stitch, this boot is made with a level of care that mass production can’t match.
The Madison St. Chukka Boot No. 5927 is for those who understand that genuine quality rarely shouts for attention. It’s a boot built to hold up over years of wear, aging gracefully rather than wearing out, and rewarding its owner with a fit and finish that only improves over time.

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